Acetone → 6-(5-ethyl-1H-pyrazol-4-yl)-1,2,2-trimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

HRID 2364049Notes

Reaction equation

HRID 2364049 reaction equation
[CH2:1]([C:3]1[N:7](S(N(C)C)(=O)=O)[N:6]=[CH:5][C:4]=1[C:14]1[S:22][C:21]2[C:20](=[O:23])[NH:19][C:18]([CH3:25])([CH3:24])[N:17]([CH3:26])[C:16]=2[CH:15]=1)[CH3:2].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+].CC(C)=O.[O-]S([O-])(=O)=O.[Mg+2].CC1C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C>[CH2:1]([C:3]1[NH:7][N:6]=[CH:5][C:4]=1[C:14]1[S:22][C:21]2[C:20](=[O:23])[NH:19][C:18]([CH3:25])([CH3:24])[N:17]([CH3:26])[C:16]=2[CH:15]=1)[CH3:2]

Participants

8

Reactant 6

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 6422Trifluoroacetic acidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium Bicarbonate2×HCID 667436105-ethyl-N,N-dimethyl-4-(1,2,2-trimethyl-4-oxo-1,2,3,4-tetrahydrothieno[3,2-d]pyrimidin-6-yl)-1H-pyrazole-1-sulfonamide

Product 1

HCID 667438776-(5-ethyl-1H-pyrazol-4-yl)-1,2,2-trimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-oneYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-ethyl-N,N-dimethyl-4-(1,2,2-trimethyl-4-oxo-1,2,3,4-tetrahydrothieno[3,2-d]pyrimidin-6-yl)-1H-pyrazole-1-sulfonamide (129 mg, 0.325 mmol) and TFA (2.00 mL, 26.0 mmol) was stirred for 1 h at room temperature. The mixture was poured into saturated aqueous NaHCO3 and extracted with EtOAc, and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was mixed with acetone (5 mL, 68.1 mmol), MgSO4 (78 mg, 0.649 mmol), PTSA (6.2 mg, 0.032 mmol) and DMF (1 mL). This mixture was stirred at 60° C. for 1 h. The mixture was poured into saturated aqueous NaHCO3 and extracted with 3:1 EtOAc/THF, and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, hexane to EtOAc then to 80:20 EtOAc/MeOH). The obtained solid was triturated with EtOAc and collected by filtration to afford the title compound (41.2 mg, 44%) as a pale yellow solid:

Workup

  1. extractionextracted with EtOAc
  2. dry with materialthe extract was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. stirringThis mixture was stirred at 60° C. for 1 h
  6. extractionextracted with 3:1 EtOAc/THF
  7. dry with materialthe extract was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography (Purif, silica gel, hexane to EtOAc
  11. customThe obtained solid was triturated with EtOAc
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-6c08ca758d4344a79aa297727e9070aa
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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